FENOPROFEN CALCIUM ANHYDROUS

Details

Stereochemistry	RACEMIC
Molecular Formula	2C15H13O3.Ca
Molecular Weight	522.602
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FENOPROFEN CALCIUM ANHYDROUS

Structure Search

SMILES

[Ca++].CC(C([O-])=O)C1=CC=CC(OC2=CC=CC=C2)=C1.CC(C([O-])=O)C3=CC=CC(OC4=CC=CC=C4)=C3

InChI

InChIKey=VHUXSAWXWSTUOD-UHFFFAOYSA-L

InChI=1S/2C15H14O3.Ca/c2*1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13;/h2*2-11H,1H3,(H,16,17);/q;;+2/p-2

HIDE SMILES / InChI

Molecular Formula	Ca
Molecular Weight	40.078
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C15H13O3
Molecular Weight	241.2619
Charge	-1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.drugbank.ca/drugs/DB00573
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/fenoprofen.html

Fenoprofen is a propionic acid derivative with analgesic, antiinflammatory and antipyretic properties. Fenoprofen inhibits prostaglandin synthesis by decreasing the enzyme needed for biosynthesis. In patients with rheumatoid arthritis, the anti-inflammatory action of fenoprofen has been evidenced by relief of pain, increase in grip strength, and reductions in joint swelling, duration of morning stiffness, and disease activity (as assessed by both the investigator and the patient). In patients with osteoarthritis, the anti-inflammatory and analgesic effects of fenoprofen have been demonstrated by reduction in tenderness as a response to pressure and reductions in night pain, stiffness, swelling, and overall disease activity (as assessed by both the patient and the investigator). These effects have also been demonstrated by relief of pain with motion and at rest and increased range of motion in involved joints. In patients with rheumatoid arthritis and osteoarthritis, clinical studies have shown fenoprofen to be comparable to aspirin in controlling the aforementioned measures of disease activity, but mild gastrointestinal reactions (nausea, dyspepsia) and tinnitus occurred less frequently in patients treated with fenoprofen than in aspirin-treated patients. It is not known whether fenoprofen causes less peptic ulceration than does aspirin. In patients with pain, the analgesic action of fenoprofen has produced a reduction in pain intensity, an increase in pain relief, improvement in total analgesia scores, and a sustained analgesic effect. Indicated for relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Also for the relief of mild to moderate pain.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00573	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Palliative	Approved 8429	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1976
Rheumatoid arthritis 316 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Primary	Approved 8429	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1976
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Primary	Approved 8429	NALFON Approved Use NALFON is a nonsteroidal anti-inflammatory drug indicated for: • Relief of mild to moderate pain in adults. • Relief of the signs and symptoms of rheumatoid arthritis. • Relief of the signs and symptoms of osteoarthritis. Launch Date 1976

C_max

Value	Dose	Co-administered	Analyte	Population
28.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
105.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/501526/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		FENOPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
400 mg 3 times / day steady, oral Recommended Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	unhealthy n = 6786 Health Status: unhealthy Condition: rheumatoid arthritis\| osteoarthritis Population Size: 6786 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf	Disc. AE: Reaction gastrointestinal, Reaction skin... Other AEs: Dyspepsia, Nausea... AEs leading to discontinuation/dose reduction: Reaction gastrointestinal (2%) Reaction skin (1%) Cardiovascular disorder (NOS) (0.5%) Other AEs: Dyspepsia (10%) Nausea (7.7%) Constipation (7%) Vomiting (2.6%) Abdominal pain (2%) Diarrhea (1.8%) Headache (8.7%) Somnolence (8.5%) Dizziness (6.5%) Tremor (2.2%) Confusion (1.4%) Sweating increased (4.6%) Pruritus (4.2%) Rash (3.7%) Tinnitus (4.5%) Blurred vision (2.2%) Hearing decreased (1.6%) Palpitations (2.5%) Nervousness (5.7%) Asthenia (5.4%) Peripheral edema (5%) Dyspnea (2.8%) Fatigue (1.7%) Upper respiratory infection (1.5%) Nasopharyngitis (1.2%) Gastritis (<1%) Ulcer peptic with perforation (<1%) Ulcer peptic with perforation (<1%) Gastrointestinal hemorrhage (<1%) Anorexia (<1%) Flatulence (<1%) Dry mouth (<1%) Blood in stool (<1%) Alkaline phosphatase increased (<1%) LDH increased (<1%) SGOT increased (<1%) Jaundice (<1%) Cholestatic hepatitis (<1%) Buccal mucosa aphthous ulceration (<1%) Taste metallic (<1%) Pancreatitis (<1%) Atrial fibrillation (<1%) Pulmonary edema (<1%) Electrocardiogram change (<1%) Supraventricular tachycardia (<1%) Renal failure (<1%) Dysuria (<1%) Cystitis (<1%) Hematuria (<1%) Oliguria (<1%) Azotemia (<1%) Anuria (<1%) Nephritis interstitial (<1%) Nephrosis (<1%) Acute papillary necrosis (<1%) Angioedema (<1%) Purpura (<1%) Bruising (<1%) Hemorrhage (<1%) Thrombocytopenia (<1%) Hemolytic anemia (<1%) Aplastic anemia (<1%) Agranulocytosis (<1%) Pancytopenia (<1%) Depression (<1%) Disorientation (<1%) Seizures (<1%) Trigeminal neuralgia (<1%) Burning tongue (<1%) Diplopia (<1%) Optic neuritis (<1%) Exfoliative dermatitis (<1%) Toxic epidermal necrolysis (<1%) Stevens-Johnson syndrome (<1%) Alopecia (<1%) Anaphylaxis (<1%) Urticaria (<1%) Malaise (<1%) Insomnia (<1%) Tachycardia (<1%) Personality change (<1%) Lymphadenopathy (<1%) Mastodynia (<1%) Fever (<1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017604s046lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A9 116 UGT2B7 146	CYP1A2 1054 CYP2C8 693 CYP2E1 667 UGT2B7 389

Drug as perpetrator

Target	Modality	Activity
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A4 80	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9004453/	yes
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23362865/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5004	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5004
ChemicalBook	CB3290884	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3290884
MolPort	MolPort-003-666-345	https://www.molport.com/shop/molecule-link/MolPort-003-666-345
eMolecules	901876	https://www.emolecules.com/cgi-bin/more?vid=901876

PubMed

Title	Date	PubMed
Agranulocytosis associated with fenoprofen.	1979 Jun 22	156260
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Enantioselective inhibition of the binding of rac-profens to human serum albumin induced by lithocholate.	2001 Jul	11400191
[Chiral separation by capillary electrochromatography on stationary phase adsorbed with protein].	2001 Sep	12545430
Analysis of acidic drugs in the effluents of sewage treatment plants using liquid chromatography-electrospray ionization tandem mass spectrometry.	2002 Apr 5	12064526
Capillary electrochromatographic separation of non-steroidal anti-inflammatory drugs with a histidine bonded phase.	2002 Dec 27	12489886
Macromolecular prodrugs: X. Kinetics of fenoprofen release from PHEA-fenoprofen conjugate.	2002 Jul 25	12100850
Renal papillary necrosis.	2002 Nov-Dec	12512867
Physical stability and solubility of the thermotropic mesophase of fenoprofen calcium as pure drug and in a tablet formulation.	2002 Oct 24	12429493
Determination of acidic pharmaceuticals, antibiotics and ivermectin in river sediment using liquid chromatography-tandem mass spectrometry.	2003 Dec 22	14735982
Enhancement of selectivity and resolution in the enantioseparation of uncharged compounds using mixtures of oppositely charged cyclodextrins in capillary electrophoresis.	2003 Jan	12569526
Optimization of sample stacking for the simultaneous determination of nonsteroidal anti-inflammatory drugs with a wall-coated histidine capillary column.	2004 Feb	14981683
Application of capillary electrophoresis with different sample stacking strategies for the determination of a group of nonsteroidal anti-inflammatory drugs in the low microg x L(-1) concentration range.	2004 Feb	14760634
Influence of rheumatoid arthritis in the enantioselective disposition of fenoprofen.	2004 Nov	15390088
Cationic vesicles as chiral selector for enantioseparations of nonsteroidal antiinflammatory drugs by micellar electrokinetic chromatography.	2004 Sep 3	15453427
Using terahertz pulsed spectroscopy to quantify pharmaceutical polymorphism and crystallinity.	2005 Apr	15736195
Effects of non-ionic surfactants on isotachophoretic separations of 2-arylpropionic acids.	2005 Aug 19	16114248
Pharmaceutical liquid crystals: the relevance of partially ordered systems.	2005 Sep	16052511
Optimization of gas chromatographic method for the enantioseparation of arylpropionic non-steroidal anti-inflammatory drug methyl esters.	2005 Sep 15	15950426
The inflammatory process of gout and its treatment.	2006	16820042
Antioxidant activity and inhibition of human neutrophil oxidative burst mediated by arylpropionic acid non-steroidal anti-inflammatory drugs.	2006 Aug	16880623
Pharmacodynamics, chiral pharmacokinetics, and pharmacokinetic-pharmacodynamic modeling of fenoprofen in patients with diabetes mellitus.	2006 Nov	17050798
Prophylaxis of migraine.	2006 Sep	19412475
The aryl propionic acid R-flurbiprofen selectively induces p75NTR-dependent decreased survival of prostate tumor cells.	2007 Apr 1	17409433
A peripatetic pediatrician's journey into pediatric rheumatology: Part II.	2007 Jun 21	17584931
Fenoprofen and ketoprofen amides as potential antitumor agents.	2007 Mar	17441909
Traditional nonsteroidal anti-inflammatory drugs and postmenopausal hormone therapy: a drug-drug interaction?	2007 May	17518513
Rapid online-SPE-MS/MS method for ketoprofen determination in dermal interstitial fluid samples from rats obtained by microdialysis or open-flow microperfusion.	2007 May 1	17227721
Peroxisome proliferator-activated receptors in the modulation of the immune/inflammatory response in atherosclerosis.	2008	18769491
Role of peroxisome proliferator-activated receptor gamma and its ligands in the treatment of hematological malignancies.	2008	18528522
Species differences in inhibition potential of nonsteroidal anti-inflammatory drugs against estradiol 3beta-glucuronidation between rats, dogs, and humans.	2008 Jul	17763456
Evaluation of pharmaceuticals and personal care products as water-soluble molecular markers of sewage.	2008 Sep 1	18800500
Synthesis and biological evaluation of O-methyl and O-ethyl NSAID hydroxamic acids.	2009 Oct	19772490
Ibuprofen-arginine generates nitric oxide and has enhanced anti-inflammatory effects.	2009 Oct	19539763
Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (S)-profens.	2010 May 5	20377222
Evaluation of phenoxybenzamine in the CFA model of pain following gene expression studies and connectivity mapping.	2010 Sep 16	20846436

Patents

Sample Use Guides

In Vivo Use Guide

400 mg to 600 mg orally 3 or 4 times a day -Maximum dose: 3200 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:49:47 GMT 2023` Edited by `admin` on `Fri Dec 15 15:49:47 GMT 2023`
Record UNII	8R95A3O51K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FENOPROFEN CALCIUM ANHYDROUS

Common Name

English

CALCIUM FENOPROFEN

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, CALCIUM SALT

Common Name

English

CALCIUM FENOPROFEN ANHYDROUS

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, CALCIUM SALT (2:1)

Common Name

English

2-(3-PHENOXYPHENYL)PROPIONIC ACID CALCIUM SALT

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-3-PHENOXY-, CALCIUM SALT, (±)-

Common Name

English

Code System Code Type Description

CAS

1260485-60-6